


Daddy and Mommy's pretty baby

by Cagedandfree



Series: Good boys for Dean [4]
Category: Supernatural
Genre: Age Play, Anal Fingering, Anal Plug, Anal Sex, Baby Sam, Castiel is a Sweetheart, Castiel is a good boy, Cock Cage, Cock Warming, Consensual spanking, Cuddling & Snuggling, Daddy Dean, Daddy Issues, Daddy Kink, Dean is a Sweetheart, Diapers, Dom Dean, Dom/sub, Feminization, Feminization Sam, I'll add more - Freeform, Infantilism, M/M, Mommy Castiel, Mommy Issues, Pacifiers, Pretty princess Sam, Rimming, Shaving, Sounding, Spanking, Sub Sam, Switch Castiel, Watersports, breastfeeding from a bra, piss drinking, sexual age play
Language: English
Status: Completed
Published: 2018-01-15
Updated: 2018-01-20
Packaged: 2019-03-05 01:17:03
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 7
Words: 5,554
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13377048
Author URL: https://archiveofourown.org/users/Cagedandfree/pseuds/Cagedandfree
Summary: Sammy wants to be a pretty princess, but Dean and Castiel feel he needs to be a pretty baby.fourth installment.read tags





	1. Chapter 1

**Author's Note:**

> I hope you enjoy

Being a pretty girl worked for a while, but slowly Dean and Castiel noticed Sam start to almost regress. They drove to a cabin where no one would be around for miles.

“He did wet the bed the other night.” Castiel pointed out.

“Yeah” Dean said placing his head in his hands. Castiel rubbed his back. 

“Honey, you had a rough childhood. Hell, you were barely children. I have an idea, but you need to stay with me. We need to both agree.”

“I’ll try anything, baby” Dean said looking at Castiel.

“I think our girl should be our pretty baby. Diapers, pacifiers. This will mean we’ll have to forgo the plug and lighten up a little bit on the cage, but Dean. If our girl was a baby, for half a year.”

“What about hunting?” 

“We’ll talk to him about that. But it may make Sammy feel safer.”

“Yeah. I agree.” Dean nodded and Castiel kissed Dean’s lips. 

Dean and Castiel walked into the bedroom where Sam was looking at himself in the mirror.

“Princess, come sit on daddy’s lap.” Sam walked over and sat on Dean’s lap.

“Am I in trouble daddy?” he asked, voice going childlike.

“No, sweetheart. Mommy and daddy have noticed that our pretty girl has regressed a bit. Is that true? Princess are you regressing?”

“Yes, daddy” Sam looked down and Castiel stroked his cheek.

“There’s no shame in that, baby girl. No shame in that at all.”

“We were thinking that maybe our good girl could be a pretty baby. Would you like that?” 

“A baby?” Sam whispered.

“Mmm hmm. Mommy and daddy would diaper you, give you a pacier.”

“What about my panties?” 

“Sweetheart, we think will be best for you.”

“Is this because of the accident the other night?” Sam started to cry and Dean held him close.

“Do you trust mommy and daddy?” Castiel whispered.

“Yes” Sam said.

“Then, we think that for now, our pretty princess should be a pretty baby. You will use the diaper. We will change you, feed you, and burp you.”

“Can I have floral onesies?” Sam asked hopeful

“Of course you can, sweetie.” Castiel smiled.

“You’re still our girl, Sammy. Just going to be doing baby things for a while.” Dean explained.

“And I’ll be cuddled?”

“Oh yes.” Dean said kissing Sam’s cheek. 

“Okay daddy, mommy. I’ll be a baby” Sam smiled.

“Good girl.”

“You’ll have a few more days of being a pretty girl. We’ll need to get our room ready.” Castiel said.

A few days later Dean and Castiel had set up a changing table in their bedroom and a crib with a mobile. Dean gave Sam a bath. Wiping his face clean of makeup. When he was dried and shaved Dean brought Sam to the changing table and placed him down. 

“Aw, baby you’re a good girl.” Dean cooed. He placed a diaper under Sam’s butt and sprinkled powder before doing it up. Dean grabbed the floral onesie and put it on Sam, snapping it up. He placed pink mittens on Sam’s hands and lifted his brother in his arms.

“Mmm, daddy, I’m a baby” Sam smiled.

“Yes you are, princess.” Dean kissed Sam’s lips and then grabbed a pacifier and placed it in Sam’s mouth. He cradled his brother and brought him to the living room where Castiel was. Sam gasped. Castiel was sitting down with some bra on. It had bags of milk inside with little nipples sticking out. Cas had it specially made.

“Hey, baby girl. I’m going to feed you.” Castiel cood. Dean took Sam’s pacifier out and placed Sam laying down on Castiel’s lap. “Come on, baby. Mommy needs you to drink” 

Sam latched his mouth around the one nipple and started to drink. Castiel cradled him and Dean rubbed Sam’s back.

“Good girl. Good baby” Dean whispered.

Dean moved Sam to the other nipple and he drank. When he was done, Dean lifted Sam in his arms and bounced him, patting his back. Castiel took the bra off.

“Come on, little baby. Give a burp for daddy.” Sam burped and Dean smiled. “Good girl” Dean placed the pacifier back in Sam’s mouth. Dean held him close. “Daddy’s got you. You’re safe.” He whispered.

Sam felt safe in his daddy’s arms. Dean kissed Sam’s temple and placed him down on the blanket Castiel had laid out. Castiel stroked Sam’s hair, leaning down to kiss him. Dean rubbed Sam’s diaper.

“Mommy and daddy expect you to use theses like a good girl” Dean smiled and Sam giggled hiding behind his mitten covered hands. 

“Baby girl, you are so cute. So very pretty. We’re going to take you for a walk, would you like that?” Castiel asked.

“yeth mommy” Sam said around the pacifier.

“Alright, pretty girl, daddy needs to get mommy ready for the walk. His good boy needs to be ready.” Dean cooed and Sam rolled on his stomach and giggled. Castiel rubbed his back. 

“We will be right back, baby” 

Dean placed the baby gate so Sam couldn’t escape and he and Castiel went to the bedroom. Castiel had given himself and enema before feeding Sam. He stripped his pants and laid down on the bed. Dean got the cock cage, tube with plug.

“Hmmph” Castiel grunted as Dean inserted the tube into his tip.

“I’m sorry, baby boy” Dean soothed.

Once the cage was on, Dean put the plug in and Castiel blushed. Dean helped Castiel put his pants on. 

“Now, you let me know when you’re going, okay?” 

“Yes sir.” Castiel smiled.

“You’re a good boy.” Dean smiled

“DAAAADDDY!!!” Sam called.

“Coming, pretty girl.” Dean called back. 

He lifted Sam in his arms when he walked into the room. Sam was crying a bit.

“Aww, princess, daddy is sorry he had to leave. Daddy’s sorry.” Dean said lifting him in his arms. Sam clung tight to him. “Shhhh. Daddy’s right here.” 

Sam gasped when he saw Castiel bring a stroller in for him.

“Look what mommy bought you” Castiel smiled.

Dean placed Sam down and strapped him in. He reached down and put on booties and covered him up with a blanket. He reached over and pulled out a frilly bonnet.

“Daddy’s princess needs to keep the sun out of her eyes.” He cooed tying it on Sam’s head. 

Castiel had packed the baby bag and Dean packed is own bag. They were going to have a little picnic.


	2. Chapter 2

Dean pushed the stroller outside and Sam giggled. When they got to the spot there was a picnic table. Dean placed the table cloth down while Castiel lifted Sam out of the stroller.

“Hey baby girl” He cooed. “Are you our pretty girl?” Sam nodded.

“Yes you are” Dean cooed leaning over and wiggling Sam’s foot. 

Castiel held Sam on his lap and Dean fed Sam homemade baby food. Finally it was time to feed Sam again. Dean took Sam from Castiel while Cas put the bra on. Castiel sat on the picnic table and Dean laid Sam across his lap. Sam happily latched on. 

“You’re a good girl, drinking from mommy.” Dean praised.

“You like is sweetie? You like the bra I had made especially for you?” Sam took his mouth off and smiled. 

When Sam had finished eating, Dean lifted him up and patted his back.

“I need to pee” Dean said still holding Sam.

“Of course” Castiel smiled.

Dean peed down Castiel’s throat and Sam finally burped. Castiel did Dean’s pants up and cleared the table. Dean placed Sam down.

“Did you use your diaper, princess?” Dean asked unsnapping the onesie and feeling around. Sam bunched up his face and bent his legs. “Oh. Is daddy’s princess going to make a poopy?” Dean cooed. 

The boys watched as Sam filled dis diaper. He started to cry and Castiel was kissing his forehead and pacifier.

“Not to worry, baby girl, daddy will clean your bum-bum” Castiel whispered. 

Dean grabbed the changing mat and lifted Sam’s legs placing it under him. He slipped on latex gloves and rolled the onesie up past Sam’s chest. Castiel took one of Sam’s mitten covered hand and held it. Dean took the diaper off and smiled.

“My girl make a big stinky. Daddy is so proud of you.” Dean praised.

With one hand Dean held Sam and he wiped him with the other. He placed a new diaper under Sam’s bottom and sprinkled the powder and did the diaper up. He snapped the onesie back up and took the gloves off. Dean lifted Sam back in his arms. 

“There princess. That wasn’t so bad. Remember, you’re a baby and we will change you.” Sam nodded and Dean bounced him a bit. 

“Dean, I-um-I.” Castiel said. Dean cradled Sam’s head to his cheek so he wasn’t looking.

“Undo your pants and show me like a good boy” Dean said and Castiel did.

When they got back to the house, they put Sam down for a nap. Dean got Castiel out of the cock cage and tube and had him hold in his pee. 

“Sir!” Castiel cried out. Dean ran a hand up Castiel’s neck.

“Shhh. You don’t want to wake the baby” Dean whispered. “Now, hold it in until you get to the toilet.”

Castiel made his way to the bathroom and released in the toilet. Dean knelt in front of Castiel, he had gloves on and lifted up is cock. He brushed his thumb against Castie’s tip. 

“Sir?” Castiel asked.

“I think we try sounding. What do you say, baby boy?”

“Sound-sounding?” Castiel squeaked.

“Mmm hmm. You already wear one with your cage. I think it can be very pleasurable.” Castiel nodded.

When Dean cleaned Castiel he had him lay on the bed. Dean grabbed the sounding kit he bought and pulled gloves on. He pulled the second smallest sound and walked over to Castiel’s head to show.

“I’m just going to try it, see how you react.” Castiel nodded.

Dean had a chair at the end of the bed, where Castiel was. Dean rolled the sound in his hands to warm it up a bit. He grabbed the medical lube and squirted some on Castiel’s tip and the on the sound. He gipped Castiel’s cock holding it straight.

“Alright, nice slow breaths for me.” Dean instructed.

“Hnnn” Castiel whimpered gripping the sheets as Dean inserted the sound.

“There’s a good boy.” He praised Castiel. Dean started to move it in and out a bit.

“Hnn” Castiel whimpered again not wanting to wake the pretty baby. 

“That’s it. Good boy.”

Dean pulled the sound out. He placed it down and stroked Castiel’s cock. Castiel was hard and Dean couldn’t have his boy release. Dean had a mini fridge with a freezer in the room. He went and grabbed an ice pack and wrapped it around Castiel’s cock.

“Ah!” the older man cried out. 

“Shhhh. Baby, I’ve got you.”

“Please sir. Please. Let me cum.” Castiel begged.

“I can’t do that, baby boy.” Dean watched as Castiel’s hard on went down. He took the ice pack off. “Such a good boy for me. Now.” 

Dean changed his gloves and put Castiel’s cock cage back on with the sound. Sam started to cry a bit.

“Daddy, mommy. I went pee-pee” the pretty baby whimpered.

“Mommy needs her rest, princess. Daddy will take good care of you.” Dean said, taking the gloves off.

Dean stroked Castiel’s head and kissed his lips before donning a new pair of gloves and going over to the crib. Dean lifted Sam out and kissed his forehead. He placed Sam on the changing table and unsnapped the onesie.

“My pretty girl went pee-pee? What a good princess you are.” Dean praised as he got the diaper off of Sam.

Dean wiped Sam and placed him in a new diaper. He took the gloves off and lifted Sam up. He stroked Sam’s cheek and kissed his pacifier.

“Mommy and daddy were playing a bit. Yes we were. Yes we were” Dean said in baby talk. Sam held up his mitten covered hand. “Oh. No, those stay on. We don’t want our pretty princess to scratch herself.”

“Will you play with me, daddy?” Sam asked.

“Oh, sweetheart. Daddy just you in a fresh diaper. Later on, okay?” 

“Will you hold me for a long time?” Sam whimpered and Dean sat on the bed next to Castiel, holding Sam tight to him and running his hands through Castiel’s hair. 

“Yes, princess.” Dean whispered patting Sam’s covered butt.

**Notes for the Chapter:**

> Anything you want to see?


	3. Chapter 3

“Oh baby girl” Castiel cooed wiping Sam. “You’re such a good girl. You are a good baby for us.”

“Daddy” Sam moaned and Dean leaned down and kissed Sam’s forehead, while rubbing his nipple. His onesie was off.

“Princess, can’t wait for you to be a pretty girl again. Daddy’s going to keep these all nice and pumped for you. You’ll have the prettiest tittes.” 

Sam gasped when he felt Castiel’s gloved finger rub against his hole.

“Princess, you’ve have been such a good baby these past few weeks. Mommy and daddy and going to play with you, but first you need and enema.” Castiel explained pulling his finger out and slipping the tube in.

Sam started whimpering and Dean soothed his princess by running his hands through Sam’s hair. Castiel started the flow of the water and took his gloves off. He walked over and started to massage Sam’s stomach. 

“It’s going to be a bit uncomfortable, sweetheart. We’re going to keep it plugged in and you’re going to have to hold it for a bit.” Dean whispered.

“Daddy, please” Sam whispered.

“Sorry, baby girl, but if daddy is going to lick your pretty pussy, it needs to be clean.” Castiel soothed.

Dean had already cleaned out Castiel. Castiel put gloves on, pulled the tube out and put the plug in, doing up Sam’s diaper. His stomach was sticking out a bit. Dean rubbed it.

“So full” Sam cried. 

“Shh, baby” Dean comforted, placing a hand on Sam’s stomach. Castiel went to Sam’s head and started to give a little head massage. 

A few minutes Sam was lifted bridal style to the bathroom, without the pacifier by Dean. Dean slipped on gloves and took Sam’s diaper off, Sam was on the toilet. Dean lifted Sam and bit, pulled the plug and Sam released. Water gushing and he started to cry. Dean placed his gloved hands on either side of Sam’s face and placed little pecks to his lips. 

“Who’s daddy’s good girl? Who’s daddy’s good girl?” he cooed

“I am” Sam whimpered.

Sam was carried back to the changing table and diapered, putting a fresh new onesie on. A nice light pink one with ruffles on the butt. Dean put Sam’s hair in pigtails and lifted Sam in his arms, placing in his crib, covering him up. Castiel placed the pacifier in his mouth and handed him his stuffed moose.

When the boys saw that Sam was sleeping, Dean turned the baby monitor on and the two went to the living room. Dean told Castiel to strip.

“Sir?” Castiel asked. As Dean turned on the baby monitor and grabbed gloves and lube. He kissed Castiel.

“No, baby. Not sir.”

“Okay” Castiel smiled.

“Cleaned you out nice this morning so I can fuck you.” 

Dean pulled the latex gloves and both men stripped. Castiel got on his elbow and knees. Dean squirted lube on Castiel’s hole and started rubbing. He inserted two fingers opening Castiel up. 

“You’re so good, baby” Dean said.

When Castiel was ready, Dean lined himself up and slid in. Castiel groaned and Dean smirked. 

“Fuck, Dean.” He grunted.

“I know, baby.” The boys stopped when they heard something on the monitor. Sam was string a bit and then went back to sleep. Dean continued to move. Castiel reached a hand down and started to stroke himself.

“So-close” Castiel said.

“Me too, baby. Okay, cum” Dean said and Castiel did.

Dean shortly behind him, spilling in Cas. The boys stayed like that for a moment and then Dean pulled out. They got cleaned up and Castiel motioned for Dean to lay in his arms.

“Come here” he said to the younger man and Dean crawled into Castiel’s arms. Castiel stroked Dean’s hair and pulled him close. “Thank you for letting me cum.”

“You’re a good boy.” Dean said closing his eyes a bit.

The two stayed like that for fifteen minutes before Sam started to whimper and sit up.

“Mommy, daddy.” He said.

“Hey pretty girl” Dean cooed getting up and walking over to the crib. 

Dean stroked Sam’s hair and scratched behind his ear. Sam leaned into Dean’s touch and reaches out to touch Dean’s cock. Dean lightly holds Sam’s wrist.

“No, princess. Daddy and mommy were fucking. This is not for you to touch.” Sam nodded.

Castiel walked over also naked. Castiel nibbles at Sam’s neck lightly sucks on Sam’s earlobe. 

“Are you ready for daddy to eat you?” Castiel whispered in Sam’s ear and Sam nodded blushing. 

“Yeah? Come on, sweetheart” Dean smiles. 

Dean lifted Sam out of the crib his legs wrapping around his older brother’s waist. Dean patted Sam’s butt a few times. Dean rubbed his nose with Sam who giggled. He placed Sam on the bed and Castiel unsapped the onesie and felt around the diaper. 

“You’re all dry” he cooed, unstrapping the diaper. Dean put gloves on and knelt down between Sam’s legs. 

“Are you ready, pretty girl? Are you ready for daddy to eat your little pussy” Dean said, rubbing a finger against Sam’s hole.

“Hmm. Daddy, please.” Sam whimpered. 

Dean leaned down and started to lick Sam. Castiel leaned down and started to kiss Sam, stroking his hair.

“Play with your little titties baby girl” Castiel whispered against Sam’s lips.

Sam started moaning, with Dean licking his little pussy and him playing with his nipples and Castiel making out with him. Dean reached a hand up and started to stroke his cock.

“You like that princess?” Dean asked looking up still stroking.

“Ye-yes” Sam whimpered. Castiel kept kissing Sam, and trailing kisses down the his neck. Finally Sam came. 

Castiel got Sam cleaned up and rediaperd. He lifted Sam up in his arms. Dean walked by and kissed Sam on the forehead and leaned into Castiel’s ear.

“I have to pee, but out girl needs a feeding so I have something for you.” Castiel nodded.

Sam laid across Castiel’s lap and Dean helped Castiel into the feeding bra with the new milk packs. Then Dean left and Sam oped his mouth, going to latch on. Castiel soothed his hair.

“Hang on sweetie. Daddy is getting something doe mommy.”

When Dean came back he had the chomp gag with the tube with the cock cage.

“Open up” Dean said and Castiel did. 

Dean placed the gag in Castiel’s mouth and placed the placed the cock cage on himself. Castiel guided Sam to the nipple and he started to drink while Dean peed and it went through the tube and into Castiel’s mouth.

**Notes for the Chapter:**

> let me know.
> 
> *REALLY wants fanart of last image*


	4. Chapter 4

Sam was bouncing in his oversized jolly jumper the boys bought for him. Meanwhile Dean had Castiel lying on the bed. Dean had gloves on and picked up the third sound. He lubed Castiel’s tip and the sound. He parted the tip and rubbed the sound.

“This is a bit bigger, baby boy.” Dean soothed.

“Mmm” Castiel nodded.

Dean slowly worked the sound in, Castiel gripped the sheets. He moved the sound in and out and then pushed it back in, moving it down. Castiel started to tear up, but he wasn’t in pain.

“Good boy” Dean praised as he fucked the sound in and out of Castiel.

“Sir! Please. Please” he cried.” 

Dean slowly started to stroke Castiel’s cock. He moved his hand up the shaft and Castiel started whimpering. Dean lightly massaged below the tip and Castiel came over himself. Dean slowly pulled the sound out.

“Good boy” he whispered stroking Castiel’s cock. 

“Sir.” Castiel cried.

“You did so well for me” 

“Thank you for letting me cum, sir” Castiel whimpered.

“You’re welcome”

Dean took some of Castiel’s cum on his finger and brought it to Castiel’s mouth. Castiel wrapped his mouth around Dean’s finger and sucked. Took his finger out and took his gloves off, putting on a new pair and cleaned Castiel up. 

“Daddy, I pee-pee” Sam whined.

“Aww, princess, daddy will get you, one moment” he mocked potted at Sam. He turned his attention to Castiel. “You rest a moment, baby”

Castiel smiled lazily and Dean changed his gloves once again and went over to Sam and pinched his cheeks earning a giggle for his brother. Dean lifted Sam up and brought him to the change table. Dean undid the snaps and rolled up the onesie just past Sam’s nipples. He undid the tabs and pulled the diaper down. 

“Let’s get my pretty girl changed.”

Dean lifted Sam’s cock and rested it no his stomach and Sam couldn’t help it, he peed a bit more. He gasped and giggled, peeing a bit more.

“Princess, are you peeing on yourself?” Dean cooed, grabbing a baby wipe and wiping Sam’s balls.

“Mmm, daddy. I play too” Sam smiled.

“Castiel, can you come clean our pretty baby.” 

Castiel came over and saw Sam, he stroked his hair and looked a Dean. Dean nodded. Castiel leaned down and started to lick the urine off of Sam.

“Mmm, you taste good, baby girl” Castiel smiled.

Deanwiped Sam’s cock and smiled shaking his head.

“Why doesn’t mommy go make a bath for our dirty girl” Dean smiled and Castiel nodded, smiling and going to the bathroom. “Did you like that, baby? Did you like peeing and having mommy lick it?” 

“Yes, daddy” Sam grind around his pacifier.

Dean took the pacifier out of Sam’s mouth and the mittens off. He lifted him up and walked into the bathroom seeing the nice bubble bath Castiel drew. Dean placed him in and took his gloves off.

“It appears our girl wants to play the way mommy and daddy play.” Dean said grabbing the wash cloth and body soap. 

“Does she?” Castiel cooed, kissing Sam’s head.

Once Sam was bathed and changed, he was put in his play pen with moose and his stuffed bumble bee. 

“Princess, mommy and daddy will be right back.” Dean smiled 

“Okay” Sam smiled.

Dean led Castiel to the bedroom and kissed him passionately. 

“Are you okay with this? Sam getting on our fun?” Dean asked, nipping at Castiel’s neck.

“Yes. I love it.” Castiel said.

“You’re sure? Because I think it’s great. I mean, when he was a pretty girl, that’s different.” Dean kissed Castiel’s neck, sucking on his pulse point.

“There are panties we didn’t want to ruin” the blue eyed man chuckled. Dean kissed the other side of his neck.

“Dean.” Castiel held Dean’s face in his hands. “What about a catheter? No control what so ever.”

“Yes.” Dean smiled.

**Notes for the Chapter:**

> Sammy is going in.
> 
> Anything you want to see?


	5. Chapter 5

Sam was sitting on Dean’s lap and Dean was bouncing him up and down on his knee. 

“Daddy?” Sam asked.

“Yes princess?” Dean cooed.

Sam got off Dean’s lap and knelt on the floor. Dean took in the sight before his eyes. Sam in pigtails, pink ruffled onesie, mittens and pacifier. Sam took the pacifier out. 

“Oh please! Let me play like you and Castiel. With the pee-pee. I want to play again.” Dean lifted Sam back in his arms.

“You do?” he asked stroking the younger man’s cheek.

“Yes, daddy.”

“Well, before we do that, daddy and mommy need to make sure that you are a really good baby girl.” 

“I am!” 

“I know, you are. Such a pretty girl.” 

Dean stood up and placed Sam on the changing table and Castiel walked in and kissed Sam on the forehead before placing the pacifier in his mouth.

“Sweetie, you know how mommy gave you another enema?” Castiel cooed and Sam nodded. “We talked about this baby girl; we’re putting the catheter in you. today” 

Castiel stroked Sam’s cheek as Dean undid Sam’s diaper and got everything ready for the catheter. He put latex gloves on took Sam’s cock in his hand.

“Princess, this is going to be uncomfortable. Daddy needs you to take some deep breaths.” Dean said and Sam nodded. “This is going to be cold.”

Dean took three cotton balls and moved it in circular motion, sterilizing Sam. He grabs the syringe with lube and squirts that inside Sam’s tip. Sam started whimpering , Castiel placed kisses on his forehead and stroked his hair.

“You’re doing a good job princess, so brave” Castiel praised.

Dean lubed the catheter and inserted it, slowly. Once it was in, he inflated it and inserted the water. He changed his gloves and got a fresh diaper. Castiel was still stroking Sam’s hair.

“What a good girl you are. So brave for us.” Dean praised stroking Sam’s inner thigh. “Such a good princess.” 

Dean took his gloves off and went and grabbed a pink baby doll dress with ruffles and showed it to Sam. Sam’s eyes lit up a bit and Dean smiled.   
“Yeah, our pretty girl is going to be in a baby doll dress.” Dean cooed and Sam smiled.

Castiel helped Sam sit up and Dean put the dress on Sam and lifted him in his arms. Dean nibbled at Sam’s neck and kissed his cheek.

“Daddy loves you princess.” Dean whispered.

“Giving up total control of your bladder is a beautiful thing, baby girl” Castiel smiled.

“Mommy’s going to feed you, sweetheart.” Dean said.

Castiel grabbed the bra and put it on, sitting down on the bed. Dean placed Sam down and rubbed a hand on his diaper butt while Sam started drinking. Castiel cradled Sam’s head.

“Good girl. Drink all your milk, sweetie. Mommy needs you to be a growing girl.” 

Later in the afternoon, Sam was lying on the blanket on the floor while Castiel was drinking from Dean. Sam crawled over a reached a hand up. Dean reached down and grabbed Sam’s hand. 

“How are you, princess? Is your diaper wet?” Sam nodded. “Yeah, you can’t control what your pee-pee does.” Castiel licked Dean’s tip and looked at Sam. 

“Baby girl, you want to play some more?” Castiel asked and Sam nodded. Dean lifted Sam onto his lap. 

“Yeah? What do you want to do? You want what mommy does? Fill you up with pee?”

“Yes daddy, fill my pussy” Sam whispered. 

“Hm, how about what daddy does with mommy? That special tube?”

“Oh please!” Sam begged. 

“Okay, let’s get the catheter out.” Dean whispered.


	6. Chapter 6

The catheter was out and Sam was given a thorough cleaning. He was naked, Castiel had Sam on his elbows and knees; latex gloves were on and Castiel was working three fingers in his ass.

“Mommy” Sam whimpered.

“Baby girl, mommy’s just opening your pussy so daddy can piss in it.” Dean had a glove on and was stroking Sam’s cock and running a hand through Sam’s hair.

“That’s right princess. Then you’re going to drink it, aren’t you sweetheart?” Dean cooed.

“Yes, daddy”

Castiel nodded Dean stood up and walking over. Castiel pulled his fingers out and Dean slid in. He reached down and stroked Sam’s cock.

“Mm, you like that princess, daddy playing with your clit and going to pee in your pussy?”

“Yes, daddy. Please, fill my pussy. Plug it up, I want to be a good baby for you.” 

Sam gasped when he felt Dean pee in him. Castiel changed his gloves and when Dean was finished, he plugged Sam up. Castiel got Sam in a new diaper and lifted him in his arms. 

“There’s a good girl. Mommy’s going to hold you for a few minutes before you we give you your bottle.”

Sam nodded and Dean was dressed now and placed the pacifier in Sam’s mouth. He stroked his hair and kissed Sam’s forehead.

“Who’s daddy’s good girl?” Dean whispered.

“I am” Sam whispered.

When a few minutes were up, Both men don latex gloves and Dean grabbed the funnel and baby bottle. Castiel took the diaper off and rolled Sam on his elbows and knees. He pulled the plug out Dean held the funnel up. 

Sam released Dean’s urine in the bottle and while Dean was getting the bottle ready, Castiel rediapered Sam and placed the frilly pink onesie on and a bib. Castiel got Sam in Dean’s lap. He cradled his brother and kissed his forehead.

Castiel took the pacifier our and Dean brushed the bottle against Sam’s lips and they parted, sucking on the bottle. Castiel stroked Sam’s hair. 

“There’s a good girl. Drink daddy’s pee-pee. Drink it up.” Castiel praised. Dean titled the bottle more.

“What a good girl you are princess.”

When the bottle was done, Dean lifted Sam in his arms and walked around patting his back and bouncing him. 

“Come on, burp for daddy” Sam let out a burp. 

“Did you like that, sweetie. Did you like drinking that?” 

“Yes mommy” Sam said.

“Yeah?” Dean cooed, rubbing a hand on his cheek. 

“Oh, yes. Daddy, yes!” 

“Well, how about you drink mommy’s pee from a bottle then? Hm? Daddy monitors what mommy drinks, he should monitor what his princess drinks.” Sam nodded enthusiastically. 

“Okay, sweetie. You will drink water, milk from mommy’s nipples and your juice.” Castiel smiled at Dean.

“Juice mommy’s pee-pee?” Sam asked happily.

“Yes, pretty girl. Your juice will be mommy’s pee-pee.” Dean smiled.


	7. Chapter 7

Dean was lying on the bed. Sam was lying on his chest asleep. Dean patted his princesse’s diapered botton. Sam slept with his blanky, sucking his pacifier for comfort. Castiel walked into the bedroom with the bib and bottle for Sam. 

“Princess. Princess, mommy has your juice, time to get up.” Dean whispered, running a hand through Sam’s hair.

“Msleepy, daddy” Sam mumbled. 

“Come on, sweetheart. While it’s warm.” Dean said, lifting his brother up and taking the pacifier out. 

He held the bottle while Castiel got the pink bib on Sam. Sam started to fuss, he wanted to sleep more.

“Aww, baby girl, we’re sorry. But babies have strict sleeping and eating schedules. Milk before naps, juice after.” Castiel cooed.

“Hey, how about a spanking after your bottle?” Dean smiled and Sam’s eyes lit up and he nodded.

Dean titled the bottle and Sam drank happily. When he finished the bottle Dean lifted him up, patting his back. Sam burped and Dean sat back down and laid Sam across his lap and started to spank Sam. 

“You are daddy’s good baby. You’re such a pretty princess. What a beautiful baby you are. Mommy and daddy are so proud of you. How easily you adapted to this life style and using the diapers. You’re a good girl.”

Dean placed Sam down in his play pen with his stuffies. Dean crouched down.

“We’re going back on out.” Dean cooed. Sam nodded.

Once again Sam was in the stroller with the booties, blanket and bonnet. Dean pinched Sam’s cheeks and they went out. Castiel wiggled Sam’s foot while he and Dean ate their food. Once Sam was changed put Sam back in the stroller.

“Baby, undress from the waist down. “ Dean said looking at Castiel. 

“Bu-but?” he said.

“That’s an order.” Dean said a little more sternly. 

Dean placed a blanket down and some pillows. He took Sam out of the stroller and sat him down. When he turned back Castiel was undressed. Dean grabbed the latex gloves and moose handing the stuffy to Sam.

“Over the bench.” He said snapping the gloves on.

“Yes, sir” Castiel said, leaning on the blanket that Dean had laid out.

“Daddy?” Sam asked.

Dean grabbed the lube and looked over at Sam.

“Princess, mommy misbehaved the other night, so daddy needs to punish him.” Dean said and Sam nodded, leaning back on the pillows and holding moose.

Dean poured lube on Castiel’s hole and on two of his fingers. He rubbed them against Castiel’s ass and eased them in. Lots of Lube.

“I need you to relax for me.” Dean said.

He slowly worked a third finger in Castiel and then a fourth and Castiel was panting.

“He-here, sir?” Castiel asked.

“Yes.” Dean said slipping his thumb in and making a fist. Dean stilled his hand and Castiel caught his breath.

“Sir, you. You can move now.” Castiel said.

“Oh, baby boy, no. There is no pleasure that you will derive from this. My hand is going to stay will in you, stretching you out for-“ Castiel looked over at the timer Dean had set up on his phone. “Ten minutes.”

When ten minutes were up and Castiel was a whimpering mess, Dean slowly eased his hand out. He lifted Castiel on the table, laying him on his side. He took his gloves off and covered him up with a blanket. Dean lifted Sam in his arms and the sat by Castiel’s head. 

“What a good boy, you are.” Dean soothed. 

That night the boys tucked their baby in and Dean held Castiel in his arms and kissed his forehead. 

“I think it’s time our baby goes back to being our pretty girl. What do you think?” Dean whispered.

“I think so too.” Castiel whispered.

**Author's Note:**

> comment, kudos suggestions


End file.
